Reacción #68768

Ecuación de reacción

water

TEMPOL

chlorambucil

DCC

DCC

chlorambucil

TEMPOL

→

Chlorambucil TEMPOL

Rendimiento 87.0%

Disolventes

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe solid materials formed
2. 2
   Filtraciónwere filtered off
3. 3
   Lavadothe filtrate was washed with 1 M HCl (1 ml)
4. 4
   SecadoThe organic phase was dried over MgSO4
5. 5
   Otroevaporated in vacuum
6. 6
   Otroto give 0.4 g of CT corresponding to a yield of 87%

Procedimiento

DCC coupling reaction was used to couple the carboxylic group of chlorambucil with the hydroxyl group of TEMPOL with the loss of a water molecule. To a stirred solution of TEMPOL (0.172 g, 1 mmol) and chlorambucil (0.304 g, 1 mmol) in methylene chloride (5 ml) at 0° C. under argon, DCC (0.206 g, 1 mmol) (Dicyclohexyl carbodiimide) and DMAP (0.0307 g, 0.25 mmol) (Dimethyl amino pyridine) were added and the reaction mixture was stirred for 12 hrs at room temperature. The solid materials formed were filtered off, and the filtrate was washed with 1 M HCl (1 ml) followed by saturated NaHCO3 (2 ml) and brine (2 ml). The organic phase was dried over MgSO4 and evaporated in vacuum to give 0.4 g of CT corresponding to a yield of 87%. TLC (Thin Layer Chromatography) of the product showed a single spot only.

Fuente